18 Fashion Designers on the First Item They Ever Sold

You might think that, in fashion, a designer's "big break" comes in the form of a splashy runway show or a big profile in a magazine. For many it certainly can—but oftentimes you’ll find that it’s the moment they sold their very first item that really sticks with them, even years later, as the moment something clicked. Think about it: With that first sale, someone is literally buying into and validating a designer’s vision and craft. Aside from being the foundation of a business, it represents something larger, and can feel just as crucial as a good review or celebrity endorsement.

We spoke to 18 fashion designers about that first. It could be the first collection they designed that made it onto store floors, or the crafts they peddled amongst encouraging family members and friends that made them a few bucks; in some cases, the item is still considered one of their signature offerings, but in others it was simply a stepping stone for growing into their own as creatives. Look back on the items that sent designers on the road to launching their namesake brands, ahead.

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“In 2001 I did an ‘I Love New York’ shirt—just for fun, I cut it up, made it a bit funky, and sent it to my dear friend Jenna Elfman. She later wore it on a Jay Leno appearance, which aired on September 13, 2001; during their interview, he asked about the shirt, and immediately it was everywhere.

“I was 21 and working for another designer—once Jenna wore the shirt on Leno, that’s when the orders started. I was so busy trying to fulfill [them], even my boss encouraged me to leave my job and start my own line. The I Love NY shirt signified the beginning of me taking that step toward being a designer. I had always loved working with patterns, constructing, and draping garments, but this was the first moment I could actually start working toward creating pieces under my name. At the time I couldn’t think about it too much as I had orders to fulfill, but it was a truly special, pivotal moment.

“Some years later Jenna called me and asked if I wanted to do a handbag for an upcoming film. I was happy to help, thinking, Why not? I’ll try a bag. That was the moment that led to the Morning After Bag. Even though it didn’t make it into the film, I planned to add it into the clothing line. I had no intention of designing handbags, but when Daily Candy wrote about it shortly thereafter, it took off—at that moment I transitioned to handbags, exclusively offering the Morning After Bag in different colorways. I kept the focus on the details (i.e., theme and story around each bag), using beautiful leathers and trims. The showroom I was with at the time told me I had to offer more than one bag, and that is where it all began.

"When I think about our current product assortment—i.e., the Feminist Tee or GRL PWR Sweatshirt—they’re the social signifiers of belonging to a community. When a woman wears Rebecca Minkoff, she knows many other women have her back. She’s confident that she’s one of many, and that together among many, she can change the world. Both the I Love NY tee and the MAB were special pieces that were meant to offer a message, whether to the world or to the individual carrying them.”

“Our classic studded Charlie boot was the first item we sold when I started the line. We also sold a couple of our biker leather jackets during that time too, which was exciting, but our Charlie boots could barely stay in stock.

“I was actually wearing the boots myself constantly and started getting a lot of attention because of them.. I remember I walked into Satine in West Hollywood, and a buyer was obsessed and put in a big order for them on the spot. Then we just put them online on our own commerce and promoted through social, and it never really slowed down since.

“I was about 29, I had just had my daughter Bianca, and I was pregnant with my son Benjamin. We moved back to L.A. from Copenhagen to build the company, and I remember feeling so positive that this was what I was meant to do.

“It was one of the first sales for the brand period, but also one of the first to really put us on the map as a legitimate line. Customers started emailing us about the shoes all the time—there was always a wait list and a demand for more. And then it really became explosive when we saw people like Jessica Alba and Gigi Hadid wearing the boots over the years. It was really an exciting time for the business. It’s still very much one of our best-sellers. We didn't expect for it to be such a long-lasting success, but obviously we’re thrilled that people keep on wanting it and identify that particular style with our core brand. It's really fun to see the sales still coming through, and more than anything, I love when I get to see it in the wild, out on the streets. It makes me so happy and makes me feel like we did something right early on.”

“I used to trek around the charity and vintage shops in east London as a student looking for old jeans. I would never pay any more than £10 for a pair, and my focus was always to find good five-pocket jeans. I would then take them home and make them into skirts on my sewing machine. I made them for myself at first—I always had a passion for denim as a base fabric, and loved the manipulations you could create in wear and wash. With each new skirt I made, my friends would clobber over each other admiring them and started asking me to make more. I started making them to borrow and eventually to sell. I was 18.

“Being fashion students, we often made and sold different styles at a local market on Sundays. There was a great one on Brick Lane, under the arches of East London.

“This sale was a pretty integral point at which I realized a true love for denim and a passion for creating and selling. The process of making something and seeing that process through to a sale solidified a desire to one day build a company. I greatly believe passion for what you do is the linchpin to the making of a great company.

“I got into denim and have spent my career creating collections for various brands in the U.S. before launching AYR. Denim has always been a huge passion of mine, especially at AYR. And seeing a smiling face come out of the dressing room with satisfaction for the product we have created is the best feeling.”

“It was my first-ever sample of my Cry Baby Necklace. I sold it to one of my best friends, Blake. I must have been 23 or so at the time—it was during the early development phases of my launch collection. She knew what I was up to at the time with Alison Lou, and she’s a bit of a drama queen so she just had to have the face; it was larger than my faces now, and the features were not as elevated. Blake was actually the inspiration behind the piece, so I still think of her whenever I look at the Cry Baby face.

“Considering the fact that Blake still comes to me for all her gifting needs, it feels so fitting that she was the right girl for my first sale. I just remember being super excited to make [it]…as I am with every sale to this day!”

“[The first item I ever sold was] a lilac-color velvet headband with aqua sequins. (Ha!)

“I always had an entrepreneurial spirit and a design sense, so when I first went to M&J Trimming, I was absolutely mesmerized: rows and rows of ribbons and trims in different sizes and textures, displayed so beautifully in every color of the rainbow. It was sensory overload, in the most dazzling way. I decided to create a collection of headbands that I DIY-ed with velvet ribbons hot-glued to elastic trim. I was 12. I sold them to my friends in middle school, and then a local boutique bought some as well—I even had linesheets! It makes me laugh now to think about it. But it wasn’t about the item itself; it was about this passion I had for entrepreneurship and it was contagious—people wanted in. In moments of doubt and challenge, I remember that this skill and passion is within me. It’s who I am and what I have always been intrinsically driven to do.”

“[For Brave Collection] it took months just to come up with this first sample—it looks so simple now! I worked with an artist locally in New York to come up with this ‘model’ that I could hone with my artisan partners in Cambodia, once I found them. While the signature Brave centerpiece (Klahan in Khmer, the language of Cambodia) is the same, the style definitely changed; our look now is a bit more raw and organic, embracing the handmade qualities of the design, instead of creating something mathematically perfect that lacks that human touch, that soul.

“I sold the first few pieces at a friends-and-family launch party in my hometown. It was definitely not a polished launch event, but more a chance to share my vision with my community, and get the support I needed to get this collection off the ground! Some of my closest friends still have these original samples from way back when.”

“[The first item I ever sold was] a woodpecker-print blouse to United Arrows in Japan. I went to the Masters in Georgia and was bored out of my mind, so I designed a print [inspired by the scene] because there are a lot of woodpeckers there—United Arrows saw it on style.com and came in. They were our first account.

“Rashida Jones was our first celebrity to wear Tanya Taylor, and she wore the woodpecker blouse when she was hosting a comedy event. It taught me that classic silhouettes with a sense of playfulness is where the brand needed to go.

“I remember it’s timelessness. People still wear it. It felt like a twist on a classic button-up.”

“[The first item I ever sold was] my diamond infinity ring, [to] a close friend. I was 26 or 27 at the time—I was just starting to explore designing jewelry as a career.

“I really wanted to design a friendship ring. I decided to intertwine two circles and create the piece in 18-karat rose gold and diamonds. I've always loved rose gold, and it has become a signature part of my line. I was exploring designing with circles and geometric shapes—it was one of my very first ring designs, and I was so proud when a friend loved it so much that she took it off my finger and bought it!

“[This sale] gave me the confidence that I could truly pursue this as a career. It gave me the courage to move forward because I realized that people would respond to my designs.”

“[The first item I ever sold were] blue skinny jeans with grommets. They were called the Brigitte, and I sold them for $250. They're still available in black, actually. It was [to] my friend—the fifth sale was a complete unknown, and it was major.

“I was working in casting at an agency. I had been there about a year—it was the end of the summer, and I was feeling creatively stunted. It was really difficult for me to be at a desk all day. As a side project, I went to Midtown and made these jeans.

“[The sale] validated exactly what I thought I needed to be doing. It was the beginning of my company, it was proof of concept, it meant something was happening.”

“The first item I ever sold was a selection of shoes from my spring 2015 collection. The inspiration was Ottoman miniature paintings and the Mermaid's Lagoon from Peter Pan. It was full of matte custom-color pastels and metallic snakeskins; we had handmade leather orchids with bendable petals, fabric flowers, and distinctive shapes. I was 22, just starting out.

“Before starting my business, I had created an excel spreadsheet of 300 stores with detailed lists of all their brands, names and contacts of buyers (I called each store personally), and the buyer's tastes and quirks. Penelope [in Brescia, Italy], was one of the stores on my list filed under ‘positioning’—it's run by a fabulous lady named Roberta with a blazing red bouffant and a [reputation] for discovering young designers who go on to make it big. The store carries some of my favorite brands like Christopher Kane, Courrèges, Jacquemus, Comme des Garcons. I just thought it would be the perfect fit. [Roberta’s] niece Marta asked via email if I could come to the store, and I immediately replied: Yes, absolutely, 100 percent. I didn’t even know where Brescia was, and I spoke almost no Italian at the time. I got on a train, and I rolled up to the store while it was closed during lunch hour. The collection was a real labor of love, and they really like all the novel silhouettes I created. It was a very positive experience. It was the first time I ever felt validated as a designer.

“Having a top Italian store was crucial in positioning me as a brand that was good on its own merit, and not just supported by family and friends back home. This was before I had any press, and years before I had any celebrity, so it was a double credit to my name. Penelope was the first real breath of life for us.”

“[The first item I ever sold was] Outdoor Voices’ Two-Tone Full Length Legging in Dove & Ash—they’re still a best-seller. They were different than anything other activewear brands were doing, and it was fun to see people resonate with a new aesthetic so quickly. They’re flattering, textured, and at the same time cozy and supportive.

“I was 25. I started [the company] out of school, and while I had some experience interning, I was really just figuring out how to do everything myself. I initially designed five pieces—a bra, leggings, crop, sweats, and hoodie—that I felt were everything you needed to start being active. I had a teeny-tiny first production line and sold with a few boutique retails, one of which was Couverture and The Garbstore in London.

“Couverture and The Garbstore has a neat assortment and at the time, we were the only activewear brand they carried. It was great for Outdoor Voices to take a different path and be merchandised alongside some of my favorite brands, like Acne and APC. Not only did it give us incredible exposure, but it’s where one of the buyers from J.Crew found Outdoor Voices and became our introduction to Mickey Drexler and Jenna Lyons. J.Crew soon placed an order for 11,000 units, which at the time was a major break for [the company].”

“[The first item I ever sold was] The Trench Dress [to] Bergdorf Goodman, after I was spotted by Roopal Patel (now the fashion director at Saks Fifth Avenue)—she was my first buyer.

“It opened the door for me. Shortly thereafter, I appeared on Oprah, thanks to Adam Glassman, in a segment entitled ‘The Next Big Thing in Fashion.’ This was a very pivotal point in my career—and as you can see in my recent release of the Angelina Trench, the trench dress inspiration is still present.”

“My very first pump was named after my grandmother, Harriet, and we sold it to Bergdorf Goodman our first season, for fall 2005. I was just starting out with my company—I think I was 29. I was very close to my grandmother growing up, and she was incredibly chic and inspiring to me. I knew I wanted to name my first shoe after her. I remember it being very comfortable, very elegant, and understated and having the perfect toe shape. We still sell our line to Bergdorf, which I think is a real testament to what we’ve been able to accomplish.”

“Beyond the lemonade stands and hand-painted seashells, the first major item I ever sold was a Jill Stuart cocktail dress in my mother’s East Hampton Jill Stuart boutique. I was working there as the store manager over the summer my freshman year of college. It was the morning of the opening, and a woman came in that needed a dress for a benefit that night. [She] summered in the Hamptons every year, but had never shopped Jill Stuart before. I was about 18 at the time, obsessed with fashion and starting my first real job as a sales associate.

“I remember that item because the woman came back later that day with her husband and bought the same dress in black, along with 10 other dresses for the rest of her summer events. It was one of my biggest sales of the summer, and I steamed and packaged each dress in a garment bag upon her request. It made me realize I wanted to make things that my customer would come back for and keep buying more of; I wanted to be a part of a woman’s everyday wardrobe.

“I learned how important it is to be consistent with your product, to experience customer feedback firsthand, and to make clothing your customer will come back for and continue to wear and support. When designing Morgan Lane, I always think about the journey each creation I design will take after it falls into the hands of its owners.”

“The first item I ever sold was an Eye See bracelet, a hand-enameled bracelet featuring two all-knowing, protective eyes. The woman who bought [it] was an acquaintance from college—we hadn't remained in touch, and I was so blown away that she could possibly want something that I made. [It] was one of the first pieces I designed—I enameled jewelry as a way to cover up the wonky seams and solder marks after my first metal working class.

“I began making jewelry when I was 27—I thought I was too old to embark on a new career and was in the midst of an existential crisis of what I wanted to do and what I was good at. I never even dreamed I could make money doing something I love!

“Selling your first piece gives you so much validation. It makes you feel like you might just have something that could resonate with other people. If I hadn't sold that piece, I might not still be making and creating. The piece was such a personal design—a reminder to trust your intuition, and the very fact that it was resonant with someone else also made me feel like creating from the heart can help heal.”

“[The first item we sold was the] Side-Zip Cashmere Sweater, in our first year of business. Our first unit went to one of our close friends, and quickly everyone on our team got one (or more, in different sizes!) for themselves.

“Modern Citizen started as a brand we built to fulfill our own need for fashion that excited us at price points we could afford, so it helped that we were our own target customer. The Side-Zip Cashmere Sweater was the first piece we were personally enamored with and that we believed could resonate with a really diverse set of women.

“At the very beginning we were hustling to learn more about our customer, and we found quickly that selling in person was a fantastic way to gauge reactions to our first products. We sold everywhere we could, from Jess's house (our first headquarters!) to office pop-up shops we called Desk to Dinner. Most of our first customers were friends and women who we reached through organic word-of-mouth, and these ladies are still our best ambassadors and VIPs to this day.

“When starting a company, there are so many days when the future seems at worst impossible and at best unclear. But the days when we're inspired, motivated, and in the zone are when we put products in the hands of our customers and they are delighted by their experience. This piece was a huge turning point—one where we knew we had hit on something special. It was our truest example of making a connection with our customer through product, and really becoming a part of her everyday life. Continuing that connection is truly what keeps us going to this day.”

“There actually isn’t one item in particular. The first collection I ever sold was spring 2017. We had a sales showroom during New York market week, and specialty boutiques and other retailers bought a selection of [it]. It was an extremely exciting feeling, knowing that our pieces would soon be sold in some of the coolest shops! I was 27 at the time—this was almost a year after I started the company and after I worked for other brands.

“The collection was very focused on exaggerated square shapes, orchid prints, and oversize silhouettes. It was [the first one] sold to stores, and we developed an ongoing relationship with these retailers and their customers. More important, I learned a lot about what each store and their customers like and dislike, and that many of the loyal customers who truly understand our brand evolve and grow with us.”

“After I graduated, I interned with our factory in Italy, where they offered to produce a small run of samples based on the designs from my graduate collection. I think we made about 10 pairs in total, and the first one I sold was a hand-crafted design made from leather and wood called the Arthouse Heel. I was 25—it was very early in my career, before launching Dear Frances. [They] went to a good friend from school.

“I adored this design. It was so full of character and hand detailing. I made a second pair after I sold the first because I desperately wanted to keep them for myself!

“The entire process was a great experience and helped me to realize that I was incredibly passionate about bringing my ideas to life and finding people who wanted to make them their own. It encouraged me to keep learning and growing with each design. Things have changed a lot since then, but it was a great springboard from theory to practice. I learned a great deal about the realities of product presentation and marketing, which is something you can’t learn in school. I realized that I loved refining and perfecting each style and how much satisfaction you can get from other people enjoying your designs.”

“I started a business making one-of-a-kind vests out of vintage scarves from the fifties and sixties that I [collected]. (Think kitschy maps of Florida, cowgirl prints from Texas, etc.) The buttons were Monopoly game pieces and dice that my father and I would drill holes through in the garage. Each vest was made up of three different patterns. I cut and sewed everything in my college dorm room, on the floor. My girlfriends seemed to like them, so I made several and took them around to a few stores.

“The first store I went to was called Knit Wit, in Boulder, Colorado. They bought all 15 pieces I had made, and subsequently put them in their storefront windows. I drove by multiple times every day for weeks! I even sold them to Fred Segal in L.A. as well as to a store in Dallas. From this experience I was forever hooked on fashion and on being an entrepreneur.”